Iodine → Methyl 5-iodo-6-methoxynaphthalene-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Iodine (7.08 g) and iodic acid (2.78 g) were added to a stirred solution of 6-methoxy-1-naphthalenecarboxylic acid methyl ester [15 g, 69.4 mmoles, described by C. C. Price et al., J. Amer. Chem. Soc., 69, 2261 (1947)] in 80% acetic acid (110 ml) and 98% sulfuric acid (0.97 ml). The solution was heated at 50° C. for 5 hr, cooled and poured into water (100 ml). After the addition of sodium bisulfite to destroy the unreacted iodine, the precipitate was collected, washed with water and recrystallized from ethanol to afford the title compound; mp 98°-99° C.; NMR (CDCl3) δ 3.95 (s, 3H), 4.00 (s, 3H), 8.00 (m, 5H).

Provenance & Evidence